John Callaway hosted Chicago Tonight for 15 years until his retirement in 1999. Then he went on to host Chicago Stories, and Friday Night, also on WTTW. He died exactly 10 years after his retirement from Chicago Tonight.

What he’s most famous for is his interviews.

V.J. McAleer, the senior vice president of production at WTTW, worked with Callaway for years.

McALEER: He could just probe and keep uncovering things. He never forgot the viewers at home had questions, and he asked questions they would ask, but he was always able to get deeper than that.
DuMONT: When newsmakers went before John Callaway, they knew they were in for a very fair but rigorous debate of the issues.

Bruce DuMont is the founder of the Museum of Broadcast Communications. He started Chicago Tonight with Callaway.

DuMONT: If they were not prepared, they were going to be eaten alive.

Callaway interviewed everyone from Mike Ditka and Oprah to Norman Mailer and Henry Kissinger. He racked up more than 100 awards, including a Peabody and 16 Emmys.

DuMont says he mentored a lot of young journalists along the way.

DuMONT: He would bring them under his wing and would nurture them, and basically would tell them when they did something good, and kick them in the pants when they did something wrong.

The current host of Chicago Tonight, Phil Ponce, says Callaway’s personality sparkled.

PONCE: He set the bar for all of us. There was no one in the building who was loved more than John Callaway. We love him, we’re going to miss him, John was our compass.

Callaway liked to tell the story of how he got started. He dropped out of college and hitchhiked to Chicago with 71 cents in his pockets. He stayed at the local Y.

In a 2001 interview on WBEZ, he said he intended to be an actor until he had this conversation with a theater director:

CALLAWAY: He said, ‘Callaway, you are the worst actor that I’ve ever had the privilege of working with and as a playwright, you’re not a lot better.’

The director pointed out that Callaway kept talking about his parents in the newspaper business.

CALLAWAY: He says there’s a place in Chicago called the City News Bureau. And he says I understand young reporters over there get to cover political events, and they get free meals. Well, the words journalism and City News Bureau didn’t mean anything to me, but the words free meals. (Laughter.)

Callaway got that job at City News. He went on to become the news director at WBBM, then vice president of CBS Radio in New York.

He started Chicago Tonight during the council wars of the Harold Washington mayoral administration to shed light on the city and politics.

Callaway explained his technique in an interview with WBEZ’s Steve Edwards:

CALLAWAY: Listening is the key to interviewing, but to do all of the work that prepares you to be other than a stenographic listener and to be profoundly, joyfully engaged in what you’re talking about.

That 1999 interview took place right before his last Chicago Tonight show.

Callaway loved music and grew up listening to Gershwin. Edwards says a few songs make him think of Callaway.

EDWARDS: One is, “Nice Work If You Can Get It.”
CALLAWAY: “Nice Work if You Can Get It.” And isn’t it true, what we do?
EDWARDS: It’s amazing. It’s the best job around.
CALLAWAY: You get a paycheck on top of it. That’s the amazing thing, because it’s just great fun.
EDWARDS: The other, as a viewer, is, “They Can’t Take That Away From Me.”
CALLAWAY (singing): “They can’t take that away from me.”
EDWARDS: We’ll miss you.
CALLAWAY: Thank you.